| 1. Round | 14/09/2019 | SSC Napoli [Youth] | - | Torino FC [Youth] | 1:0 | ||||
| 2. Round | 21/09/2019 | Bologna FC [Youth] | - | SSC Napoli [Youth] | 3:2 | ||||
| 3. Round | 28/09/2019 | SSC Napoli [Youth] | - | Inter [Youth] | 0:1 | ||||
| 4. Round | 07/10/2019 | Empoli FC [Youth] | - | SSC Napoli [Youth] | 1:1 |  |
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| 5. Round | 19/10/2019 | SSC Napoli [Youth] | - | AS Roma [Youth] | 1:2 | ||||
| 6. Round | 27/10/2019 | Chievo Verona [Youth] | - | SSC Napoli [Youth] | 1:1 |  |
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| 11. Round | 07/12/2019 | Genoa CFC [Youth] | - | SSC Napoli [Youth] | 0:3 | |
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| 12. Round | 14/12/2019 | SSC Napoli [Youth] | - | Lazio Roma [Youth] | 1:2 | ||||
| 13. Round | 22/12/2019 | Sampdoria [Youth] | - | SSC Napoli [Youth] | 2:1 | ||||
| 14. Round | 11/01/2020 | SSC Napoli [Youth] | - | Juventus [Youth] | 0:1 | ||||
| 15. Round | 19/01/2020 | Delfino Pescara [Youth] | - | SSC Napoli [Youth] | 1:0 | ||||
| 16. Round | 26/01/2020 | Torino FC [Youth] | - | SSC Napoli [Youth] | 1:2 | ||||
| 17. Round | 01/02/2020 | SSC Napoli [Youth] | - | Bologna FC [Youth] | 0:1 |  |
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| 22. Round | 06/03/2020 | ACF Fiorentina [Youth] | - | SSC Napoli [Youth] | 2:1 |
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